Stereoselective access to fluorinated and non-fluorinated quaternary piperidines: Synthesis of pipecolic acid and iminosugar derivatives

Chemistry - A European Journal

Volumn 18, Issue 12, 2012, Pages 3753-3764

  Fustero, Santos ^a,b   Albert, Laia ^a,b   Mateu, Natalia ^a,b   Chiva, Gema ^b   Mirõ, Javier ^a   González, Javier ^c   Aceña, José Luis ^b,d  

^a UNIVERSITY OF VALENCIA   (Spain)

^b CENTRO DE INVESTIGACIÓN PRÍNCIPE FELIPE   (Spain)

^c UNIVERSITY OF OVIEDO   (Spain)

^d UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

amino acids; density functional calculations; fluorine; iminosugars; quaternary stereocenters

Indexed keywords

ALKYL DERIVATIVES; AZA-MICHAEL REACTION; CROSS METATHESIS; DENSITY-FUNCTIONAL CALCULATIONS; DIASTEREOSELECTIVE; DIHYDROXYLATION; FLUORINATED DERIVATIVES; IMINOSUGARS; PIPECOLIC ACID; QUATERNARY STEREOCENTERS; REACTION MECHANISM; STEREO-SELECTIVE; SYNTHETIC INTERMEDIATES; TARGET COMPOUND; THEORETICAL STUDY; TRIFLUOROMETHYL; TRIMETHYLSILANE;

AMINO ACIDS; DENSITY FUNCTIONAL THEORY; FLUORINE; STEREOSELECTIVITY;

PIPE;

IMINOSUGAR; PIPECOLIC ACID; PIPECOLIC ACID DERIVATIVE; PIPERIDINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; HALOGENATION; STEREOISOMERISM; SYNTHESIS;

HALOGENATION; IMINO SUGARS; MOLECULAR STRUCTURE; PIPECOLIC ACIDS; PIPERIDINES; STEREOISOMERISM;

EID: 84859018873     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201102351     Document Type: Article

References (62)

1. X.-L. Qiu, W.-D. Meng, F.-L. Qing, Tetrahedron 2004, 60, 6711-6745
2. K. Uneyama, in Fluorine in Medicinal Chemistry and Chemical Biology (Ed:, I. Ojima,), Wiley, Chichester, 2009, pp. 213-256
3. C. Czekelius, C. C. Tzschucke, Synthesis 2010, 543-566
4. X.-L. Qiu, F.-L. Qing, Eur. J. Org. Chem. 2011, 3261-3278.
5. M. Zanda, New J. Chem. 2004, 28, 1401-1411.
6. A. Asensio, P. Bravo, M. Crucianelli, A. Farina, S. Fustero, J. García Soler, S. V. Meille, W. Panzeri, F. Viani, A. Volonterio, M. Zanda, Eur. J. Org. Chem. 2001, 1449-1458
7. F. Huguenot, T. Brigaud, J. Org. Chem. 2006, 71, 7075-7078
8. Q.-Q. Min, C.-Y. He, H. Zhou, X. Zhang, Chem. Commun. 2010, 46, 8029-8031
9. D. Enders, K. Gottfried, G. Raabe, Adv. Synth. Catal. 2010, 352, 3147-3152
10. R. Husmann, E. Sugiono, S. Mersmann, G. Raabe, M. Rueping, C. Bolm, Org. Lett. 2011, 13, 1044-1047
11. G. Huang, J. Yang, X. Zhang, Chem. Commun. 2011, 47, 5587-5589
12. S. Fustero, M. Sánchez-Rosellõ, C. Báez, C. del Pozo, J. L. García Ruano, J. Alemán, L. Marzo, A. Parra, Amino Acids 2011, 41, 559-573; for a review, see
13. R. Smits, C. D. Cadicamo, K. Burger, B. Koksch, Chem. Soc. Rev. 2008, 37, 1727-1739.
14. N. Margiotta, P. Papadia, F. Lazzaro, M. Crucianelli, F. De Angelis, C. Pisano, L. Vesci, G. Natile, J. Med. Chem. 2005, 48, 7821-7828.
15. D. Maisch, P. Wadhwani, S. Afonin, C. Böttcher, B. Koksch, A. S. Ulrich, J. Am. Chem. Soc. 2009, 131, 15596-15597, and references therein.
16. C. Cativiela, M. D. Díaz-de-Villegas, Tetrahedron: Asymmetry 2000, 11, 645-732
17. K.-H. Park, M. J. Kurth, Tetrahedron 2002, 58, 8629-8659
18. P. Maity, B. König, Biopolymers 2008, 90, 8-27
19. M. I. Calaza, C. Cativiela, Eur. J. Org. Chem. 2008, 3427-3448
20. C. Cativiela, M. Ordõñez, Tetrahedron: Asymmetry 2009, 20, 1-63.
21. S. Fustero, M. Sánchez-Rosellõ, V. Rodrigo, C. del Pozo, J. F. Sanz-Cervera, A. Simõn, Org. Lett. 2006, 8, 4129-4132
22. S. Fustero, M. Sánchez-Rosellõ, V. Rodrigo, J. F. Sanz-Cervera, J. Piera, A. Simõn-Fuentes, C. del Pozo, Chem. Eur. J. 2008, 14, 7019-7029
23. S. Fustero, V. Rodrigo, M. Sánchez-Rosellõ, C. del Pozo, J. Timoneda, M. Frizler, M. T. Sisay, J. Bajorath, L. P. Calle, F. J. Cañada, J. Jiménez-Barbero, M. Gütschow, Chem. Eur. J. 2011, 17, 5256-5260.
24. G. Chaume, M.-C. Van Severen, S. Marinkovic, T. Brigaud, Org. Lett. 2006, 8, 6123-6126
25. C. Caupène, G. Chaume, L. Ricard, T. Brigaud, Org. Lett. 2009, 11, 209-212
26. G. Chaume, N. Lensen, C. Caupène, T. Brigaud, Eur. J. Org. Chem. 2009, 5717-5724.
27. S. N. Osipov, C. Bruneau, M. Picquet, A. F. Kolomiets, P. H. Dixneuf, Chem. Commun. 1998, 2053-2054
28. S. N. Osipov, O. I. Artyushin, A. F. Kolomiets, C. Bruneau, M. Picquet, P. H. Dixneuf, Eur. J. Org. Chem. 2001, 3891-3897
29. M. Eckert, F. Monnier, G. T. Shchetnikov, I. D. Titanyuk, S. N. Osipov, L. Toupet, S. Dérien, P. H. Dixneuf, Org. Lett. 2005, 7, 3741-3743
30. G. T. Shchetnikov, S. N. Osipov, C. Bruneau, P. H. Dixneuf, Synlett 2008, 578-582
31. A. V. Gulevich, N. E. Shevchenko, E. S. Balenkova, G.-V. Röschenthaler, V. G. Nenajdenko, Synlett 2009, 403-406
32. M. Eckert, S. Moulin, F. Monnier, I. D. Titanyuk, S. N. Osipov, T. Roisnel, S. Dérien, P. H. Dixneuf, Chem. Eur. J. 2011, 17, 9456-9462.
33. V. De Matteis, F. L. van Delft, J. Tiebes, F. P. J. T. Rutjes, Eur. J. Org. Chem. 2006, 1166-1176
34. V. De Matteis, F. L. van Delft, H. Jakobi, S. Lindell, J. Tiebes, F. P. J. T. Rutjes, J. Org. Chem. 2006, 71, 7527-7532
35. W. B. Jatoi, A. Bariau, C. Esparcieux, G. Figueredo, Y. Troin, J.-L. Canet, Synlett 2008, 1305-1308.
36. T. Billard, B. R. Langlois, Eur. J. Org. Chem. 2007, 891-897
37. J.-A. Ma, D. Cahard, Chem. Rev. 2008, 108, PR 1 -PR 43.
38. G. K. S. Prakash, A. K. Yudin, Chem. Rev. 1997, 97, 757-786
39. R. P. Singh, J. M. Shreeve, Tetrahedron 2000, 56, 7613-7632.
40. S. Fustero, L. Albert, J. L. Aceña, J. F. Sanz-Cervera, A. Asensio, Org. Lett. 2008, 10, 605-608.
41. V. V. Levin, A. D. Dilman, P. A. Belyakov, M. I. Struchkova, V. A. Tartakovsky, Eur. J. Org. Chem. 2008, 5226-5230
42. N. E. Shevchenko, K. Vlasov, V. G. Nenajdenko, G.-V. Röschenthaler, Tetrahedron 2011, 67, 69-74.
43. F. Hein, K. Burger, J. Firl, J. Chem. Soc. Chem. Commun. 1979, 792-793
44. R. D. Chambers, Y. A. Cherbukov, T. Tanabe, J. F. S. Vaughan, J. Fluorine Chem. 1995, 74, 227-228
45. M.-H. Larraufie, C. Courillon, C. Ollivier, E. Lacôte, M. Malacria, L. Fensterbank, J. Am. Chem. Soc. 2010, 132, 4381-4387.
46. S. Fustero, N. Mateu, L. Albert, J. L. Aceña, J. Org. Chem. 2009, 74, 4429-4432.
47. L. M. Harwood, K. J. Vines, M. G. B. Drew, Synlett 1996, 1051-1053.
48. J. E. Baldwin, J. Chem. Soc. Chem. Commun. 1976, 734-736
49. J. E. Baldwin, J. Cutting, W. Dupont, L. Kruse, L. Silberman, R. C. Thomas, J. Chem. Soc. Chem. Commun. 1976, 736-738.
50. A. J. Mancuso, D. Swern, Synthesis 1981, 165-185.
51. B. S. Bal, W. E. Childers, Jr., H. W. Pinnick, Tetrahedron 1981, 37, 2091-2096.
52. Iminosugars: From Synthesis to Therapeutic Applications (Eds:, P. Compain, O. R. Martin,), Wiley, Chichester 2007.
53. R.-W. Wang, F.-L Qing, Org. Lett. 2005, 7, 2189-2192
54. R.-W. Wang, X.-L. Qiu, M. Bols, F. Ortega-Caballero, F.-L. Qing, J. Med. Chem. 2006, 49, 2989-2997
55. R.-J. Li, M. Bols, C. Rousseau, X.-G. Zhang, R.-W. Wang, F.-L. Qing, Tetrahedron 2009, 65, 3717-3727
56. R. Csuk, E. Prell, C. Korb, R. Kluge, D. Ströhl, Tetrahedron 2010, 66, 467-472.
57. 3 group has been calculated to lie between those of isopropyl and tert-butyl groups; see:, W. K. Hagmann, J. Med. Chem. 2008, 51, 4359-4369, and references therein.
58. R. P. M. Storcken, L. Panella, F. L. van Deltf, B. Kaptein, Q. B. Broxterman, H. E. Schoemaker, F. P. J. T. Rutjes, Adv. Synth. Catal. 2007, 349, 161-164; amino acid 39 and analogues containing variable chain lengths were selectively incorporated into peptidic sequences for the construction of highly stabilized α-helix structures by means of ring-closing metathesis processes
59. C. E. Schafmeister, J. Po, G. L. Verdine, J. Am. Chem. Soc. 2000, 122, 5891-5892
60. Y.-W. Kim, P. S. Kutchukian, G. L. Verdine, Org. Lett. 2010, 12, 3046-3049.
61. S. Fustero, D. Jiménez, M. Sánchez-Rosellõ, C. del Pozo, J. Am. Chem. Soc. 2007, 129, 6700-6701
62. S. Fustero, S. Monteagudo, M. Sánchez-Rosellõ, S. Flores, P. Barrio, C. del Pozo, Chem. Eur. J. 2010, 16, 9835-9845.